Pros
The beauty of working at Automattic is that you are part of a worldwide team of people who all bring their expertise, knowledge and skills to the table. You feel very connected, even though you can work from anywhere you wish. They help you set up a home office and invest in you as a person holistically. Automattic provides you with access to professional development and learning opportunities, health gear, wellness benefits and a competitive remuneration package. Automattic aims to make the web a better place and contributes 5% of their resources to the opensource WordPress project. The creed of the company really resonates with me and it is awesome to be part of a company that is dreaming big and care about their employees.
Kontras
The only con I can think of is that you need to work around employees in different time zones.